Diquaternary compounds



Patented Nov. 11, 1952 DIQUATERNARY COMPOUNDS John G. Erickson, Minneapolis, Minn., assignor to General Mills, Inc., a corporation of Delaware No Drawing. Application March 6, 1952, Serial No. 275,239

6 Claims.

The present invention relates to compounds having the following formula CH3 RNCH CH NR in which R is an aliphatic hydrocarbon group containing from 8 to 22 carbon atoms, and NR is a group selected from the group consisting of pyridine, picoline, lutidine, and collidine groups, and in which X is halogen.

These compounds are surface-active agents and emulsifying agents. Some of them are of unusual interest in that they display good foaming properties and have very desirable effects on surface tension but are not effective as wetting agents as measured by the standard canvas disk test. The compounds are also unusual in that they are found to possess good surface-active and emulsifying properties even when the fatty group is near the upper portion of the range described hereinbefore. Many compounds having fatty groups are found to be much less effective when they contain fatty groups of 18 or more carbon atoms.

It is therefore an object of the present invention to provide novel compounds having the above formula.

It is another object of the present invention to provide a, novel process of producing the same.

These compounds may be made by the following reaction:

RE TOHzCHQX R'N RNCHrCEzNR' Ha Ha The quaternary ammonium halide used as a starting material in this reaction may be prepared from fatty amines by first preparing dimethyl fatty amines by conventional methylation procedures, and then reacting the dimethyl fatty amine with an ethylene dihalide (dichloride or dibromide) in accordance with the following reaction:

CH3 RN(OHa)2+XCHzCHzX Rl fomomX CH3 The fatty amines may be derived from fatty acids and accordingly the amines employed may comprise the mixed amines derived from the mixed fatty acids of a fat or oil or from any 2 single fatty acid or any selected group of such fatty acids. The aliphatic hydrocarbon group B may be either saturated or unsaturated.

The preparation of the diquaternary compounds of the present invention may be accomplished by merely heating the monoquaternary compound with the selected pyridine compound. The pyridine compound is preferably employed in excess. The reaction is conveniently carried out on a steam bath for most of the compounds herein described. Where less reactive compounds are employed a greater degree of heat may be employed. In any event, from 10 to 20 hours at 110-120 C. is adequate for all of the compounds of the present invention. The reaction product may be isolated by chilling the reaction mixture and filtering, or by adding a liquid which will precipitate the product and then filtering the precipitated product. In addition, the products may be isolated by distilling off all volatile materials.

Erample 1 A mixture of 7.8 parts of 2-chloroethyldimethyldodecylammonium chloride and 25 parts of pyridine was refluxed (113 C.) for 7 hours. It was then cooled and acetonitrile was added. Filtration yielded N-(2-dimethyldodecylammoniumethyl) pyridinium dichloride.

Example 2 A mixture of 9.7 parts of 2-bromoethyldimethyloctadecylammonium bromide and 25 parts of pyridine was heated at -95 C. for 4 hours. The originally liquid mixture solidified as the reaction proceeded. It was mixed with ethyl acetate and filtered to yield N-(2-dimethyloctadecylammoniumethyl) pyridinium dibromide.

Example 3 A mixture of 6.2 parts of 2-chloroethyldimethyldodecylammonium chloride and 23.9 parts of gamma-picoline was heated at 70-80 C. for 6 hours. The excess picoline was then distilled off under reduced pressure. The residue was dissolved in benzene and reprecipitated by the addition of a low-boiling hydrocarbon, thus yielding N (2 dimethyldodecylammoniumethyl) 4 methylpyridinium dichloride.

In place of the fatty amine compounds specifically described in the examples, any other fatty amine compound containing a fatty group of from 8 to 22 carbon atoms, either saturated or unsaturated, may be employed. Similarly in place of the pyridine and picoline compounds speciflcally described, other pyridine compounds, such as alphaand beta-picoline, 1,2-, 1,3-, 2,4-, 2,6-, or 3,6-lutidines may be employed, as well as lutidines containing a single ethyl substituent in place of the dimethyl substituents. Similarly, collidines such as 4-ethyl-2-methylpyridine, 3- ethyl-4-methylpyridine, 2,4,6-trimethylpyridine, and other collidines containing three methyl roups, a methyl and an ethyl roup, or containin solely a propyl group. The halogen atom in these compounds may be either chlorine or bromine. With the alternative reactants listed above, the reaction proceeds in the same manner and. the same type of product is obtained.

I claim as my invention: 1. Compounds having the following formula CH: +1 RNCHZCHZNR in which R is an aliphatic hydrocarbon group containing from 8 to 22 carbon atoms, NR, is a grOup selected from the group consisting of pyridine, lutidine, picoline, and collidine groups, and X is halogen.

2. Compounds having the following formula 3 Khomeini? in which R is an aliphatic hydrocarbon group containing from 8 to 22 carbon atoms, and X is halogen.

3. N- (2-dimethyldodecylammoniumethyl) pyridinium dichloride.

4. N- (2-dim'ethyldodecylammoniumethyl) pyridinium dibromide.

5. N (2-dimethyldodecylammoniumethyl) -4- methylpyridinium dichloride.

6. Process of producing compounds having the followin formula OH: RNCHQCH NR' in which R is an aliphatic hydrocarbon group containing from 8 to 22 carbon atoms, NR is selected from the group consisting of pyridine, picoline, lutidine, and collidine groups, and X is halogen, which comprises reacting the compound CH: R i ICH2CH2X with a compound selected from the group consisting of pyridine, picoline, lutidine and collidine, and recovering the compound first named.

JOHN G. ERICKSON.

No references cited. 

1. COMPOUNDS HAVING THE FORMULA 